


Google, why does it feel good when it hurts?

by spaghedwards



Series: Google, Tell Me. [1]
Category: IT (2017)
Genre: Anal Fingering, Anal Sex, Dry Sex, M/M, Size Difference, Slight Bondage, Smut, bdsm undertones, but a soft cute freak whom i love with all my heart, hes basically a freak, if anything eddie likes it, mild pain play, slight dub con, this isn't about a rape or anything don't worry
Language: English
Status: Completed
Published: 2018-02-23
Updated: 2018-02-23
Packaged: 2019-03-22 19:10:45
Rating: Explicit
Warnings: Underage
Chapters: 2
Words: 4,453
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13770675
Author URL: https://archiveofourown.org/users/spaghedwards/pseuds/spaghedwards
Summary: Eddie was moaning loudly now, unable to do anything but just take what Richie was giving him. He couldn't stop crying or trembling. The bed began to rattle against the wall, and Richie's grunts along with Eddie's high pitched moans were filling the room. The more Eddie struggled, the more pain he felt, yet he couldn't stop scuffling. He couldn't believe how turned on he was.or the one where Eddie finds out he's kind of a pain slut.





	1. Chap 1

**Author's Note:**

> first chapter is just the flashback and explanation for chap two...

Eddie remembers what started the whole thing.

They were at Bill’s birthday party. Bill was the last one in the group to turn 17, and Stan had thrown him a surprise party at his house. When Bill finally came back from his night shift, the hiding crowd erupted and shouted ‘Surprise!’ at his very startled, terrified face. Then he began to smile, chuckling at Stan when they both shared a quick kiss.

The party went on, and loud buzz of voices and music never died down. Bill was now playing beer bong with some of the guys, and Beverly was dancing with Ben. Mike and Stan were wrestling on the floor, a bunch of people cheering them on. And Eddie and Richie--they were upstairs in one of the bedrooms, fumbling with their pants. Eddie was the first to get completely naked. He scooted up the bed and waited for Richie, letting out a frustrated whine.

"Ugh. You're so fucking slow."

Richie peeked up at him with a grin.

"I know, even your mom was telling me to go faster last night--" Eddie suddenly leaned forward and hooked his hands behind Richie's neck, kissing him. The kiss was filthy and loud, but it got Richie to finally get out of his pants, and he lunged onto him, pushing them on the bed.

Richie pulled his head back, and brought his hand up to Eddie's face, putting two fingers in his mouth. Eddie took a while to understand--the drunk state of his mind making him dumber than usual. When he did, he closed his mouth and practically slobbered on Richie's fingers. He guessed Richie forgot to bring lube--he didn't blame him though. They didn't exactly plan on fucking at Bill's birthday party.

After Richie decided it was enough, he brought his finger down to Eddie's hole and pushed in immediately. Eddie threw his head back and panted loudly, writhing around.

Usually, Richie would tease him--rubbing on his hole and licking for hours, but tonight, they were both impatient.

Richie pushed in a second finger after a minute, watching the small boy underneath him fall apart. Eddie's cheeks were red, the sweat on his forehead making some curls clump together. He was trembling, mumbling out incoherent words. He whined and pushed down on Richie's fingers, and he was becoming louder.

Richie moaned, feeling himself grown painfully hard just watching his boy respond to his fingers. It never ceased to amaze him how responsive Eddie was--to everything.

Eddie didn't know why, but at the second finger, he told Richie he was ready. Looking back, Eddie realizes that it was because he was drunk. At that state, he believed he was ready. Normally, Richie prepped him with three fingers, and for a  _much_ longer time. But that night, he made Richie stop after only five minutes. 

"Are you sure?" Richie asked him. He was looking at him with concern, but also pulling out his fingers quickly. Eddie knew he was just as desperate as he was. 

Eddie nodded, watching Richie pull out a condom from his pants on the floor. He quickly tore them open, rolling it on to his cock. Eddie moaned at the sight alone, reaching down a hand to his own cock, which was a bit red from being hard for so long. 

He never got to touch himself though--Richie quickly took his hand in his own and pressed his knuckles down next to Eddie's head. He did the same with the other hand. Eddie could only thrust his hips up now for any sort of friction. His breath hitched and he stilled his movement when he felt Richie's cock push in. 

Eddie's eyes rolled back and his head hit the bed. He felt his vision go blurry, and all Eddie remembers is the excruciating pain.

Because the thing is--and Eddie will never admit this to his boyfriend-- is that Richie is fucking  _huge._ He's 'nine and three quarters inches long', according to Richie when he measured his dick that day in Spanish class. But Eddie never knew that guys had different things happen to their cocks when they got hard. For Eddie, he grew an inch longer. But Richie--Richie didn't grow... _lengthwise_. He got so much thicker. More thick than Eddie's balled fist. That was why they had to spend so much time prepping Eddie. But that night, barely any prepping was done. 

Eddie remembers going slack after Richie pushed in. He remembers whimpering and trying to push Richie off, but he couldn't. One, because Richie was now moving his hips slowly, tucking his face into Eddie's neck, completely unaware of Eddie's struggle. Richie was drunk out of his mind, not remembering to check on Eddie before moving. Second, the music was so loud, drowning out most of the noises coming out of Eddie's mouth.

Eddie remembers tasting the salt of his tears, and the struggle against Richie's hands holding him down. Richie was now fucking him properly, thrusting his hips to meet Eddie's ass. He grunted lowly, kissing and biting at Eddie's shoulder like he always did. Eddie tried again to call out Richie's name, to get him to pull out. The pain was just too much, and it wasn't going away like it usually did.

He tried, with all his strength to get out of Richie's strong grasp, but he couldn't move at all. And then, he felt the heat pool at his lower belly. Eddie gasped, feeling a wave of arousal flow through his body. His cock was starting to throb, demanding attention. 

Eddie tried to move again, struggling like wounded animal under a predator. But Richie was fucking him faster now, the thrusts growing harsher and more animalistic. (Which only made that metaphor feel a bit too real). There was more pain now, but Eddie realized the pain was in the background now. Pleasure was taking over. It made no sense to him because this was the most painful sex that he'd ever gone through, but it was also the fucking best.

Eddie was moaning loudly now, unable to do anything but just take what Richie was giving him. He couldn't stop crying or trembling. The bed began to rattle against the wall, and Richie's grunts along with Eddie's high pitched moans were filling the room. The more Eddie struggled, the more pain he felt, yet he couldn't stop scuffling. He couldn't believe how turned on he was.

Suddenly, Eddie felt a ripple of sheer pleasure rip through his body, and thick white ropes of cum shot of his cock. He whimpered as he came, feeling the pain and stretch at his hole, but loving every second of it.

The rest of the night was a blur to Eddie. He does remember Richie finally looking at him in surprise, probably at the tears and the sudden coming with no warning. But everything else, his brain was too intoxicated to hold onto.

The next day, Eddie and Richie both woke up with massive headaches. When Eddie got up to take his Advil, he dropped back down immediately and winced at the raw ache in his hole. It hurt like hell, and Eddie felt tears well up into his eyes. But he quickly wiped them away before Richie could see. Richie said that he didn't really remember last night at all, and Eddie knew that if he told his boyfriend what happened, Richie might've never forgiven himself.

Eddie doesn't blame Richie at all; Richie was drunk, just like him. Probably even more. Eddie knows that Richie would never hurt him, unless he wanted him to. And that thought brought Eddie a week later, who was now sitting at his bed and staring at the wall.

 _Richie would never hurt me unless I wanted him to,_ he thought. 

 _Richie would only hurt me if I wanted him to._ Eddie fumbled with his fingers nervously. He furrowed his eyebrows.

 _Do I want Richie to hurt me?_ The question was lingering in the back of his mind this whole week, and it was only now that Eddie was finally answering it honestly.

He wanted it so much.  

At first, he tried to ignore the fact that he came untouched from the most painful sex ever after it happened, but every time he was with Richie, he couldn't help but remember that night. How helpless he was, how much he struggled, how much it hurt. And each time, it only made him feel aroused. 

This whole week, the group was so busy with school work; especially Eddie. This caused him to be exhausted by the time Richie came to his room. The two boys would just snuggle up together and sleep each night to make up for the time spent apart. But now it was Friday night, and Richie was coming over. Eddie's mom had gone out in a weekend spa resort, so he had the house all to himself.

Suddenly, a knock came from Eddie's window. He jumped a little, and then frowned. Richie as sitting on the roof, grinning as he watched Eddie open the window. Eddie held his breath.

How was he supposed to tell his boyfriend he wanted to be fucked raw and hard?

He let out a shaky breath as he unlocked his window. Tonight was going to be long and embarrassing for him--but hopefully, it would give Eddie the pleasure he'd been craving all week.

 

 


	2. Chap 2

"You know you could've just come through the front door. I told you Mom was gone," Eddie says as Richie comes in.

Richie take off his shoes and place it on the window sill, making sure not to get any dirt on the floor.

"Well, maybe I like climbing up to your window," Richie says. He adjust the collar of his shirt with one hand. "Makes me feel like I'm Romeo."

Eddie rolls his eyes, turning away to hide the small smile on his face. He couldn't let his boyfriend know that he actually loved all the sappy comments Richie made. Eddie feels Richie pull him back to his chest, holding him softly. 

"And you're my Juliet, my forbidden love," he pauses. He runs a hand down Eddie's bare arm, pulling a shudder from him. "So pretty, so  _soft_..." Richie bends his neck down to kiss at Eddie's neck, slowly and softly. Eddie immediately tilts his neck to give him an easier access. It seems like Richie wants to get right to business tonight, and Eddie couldn't be happier. 

He leans back against him, melting into the hard warmth of his boyfriend. The tension in his shoulders slips away as Richie rubs up and down his bare arms, fingers reaching underneath the sleeves of his t-shirt.

Richie begins mouthing at his collarbones, scraping his teeth lightly. Eddie moans at that, and the room feels much hotter now. 

"Richie..." he moans. He feels Richie's smile on his skin, and turns around to face him. He pushes him down on the bed, and quickly goes on top of him. Already, he's breathless, panting a little. 

Richie watches in amusement as Eddie slips out of all his clothes quickly. He palms at his dick through his jeans, raking Eddie up with his eyes. Eddie feels his stomach tighten momentarily when he notices the tent forming in Richie's pants. 

Eddie goes to unbutton Richie's pants, he feels a hand move his wrist away. He looks up at Richie, confused. Richie's eyes are dark and full of arousal, but there's a hint of concern--like there always is whenever they fuck. 

"Wait, let me prep you before," he says. "We haven't fucked in like, a week. You're going to need more time to prepare." 

Eddie wants to die. He stills, looking down at Richie's shirt. He knows that Richie is right; he's extremely tight right now, and Eddie thinks about the pain he'd feel without the preparation. But instead of wincing at the thought, he feels himself grow harder. And if Eddie needed any more confirmation that he wanted to be fucked raw tonight, that would be it.

_ This _   _is it,_ he thinks.  _This is where I tell him._  But somehow his brain ruins the signal to his mouth, and before Eddie can help it, he's sputtering out a lie.

 

"Oh uh. I already fingered myself." He says it too quick, too breathless. Sure enough, Richie's looking at him with a frown. 

"Really?" his tone is doubtful.

Eddie scolds himself quietly for being such a terrible liar. He nods furiously and crawls forward into Richie, sitting on his lap and placing his thighs on either side of him. Richie simply places his hands around Eddie's hips, fingers kneading Eddie's ass.

Eddie feels a bit shy being completely naked in front of the fully clothed boy. He tries to lift Richie's shirt up, but Richie's hand grips Eddie's wrist, stopping him. He swiftly moves his other hand down to his ass, finger lightly prodding at his hole.

Eddie gasps at the sudden intrusion and drops his chin down on Richie's shoulder. He lets his arms go lax, one of them still being held up by Richie near his face. He whines softly as he feels Richie rubbing the puckered surface, like he's trying to feel something. Suddenly, the finger is gone and Richie is pulling Eddie's hair gently until Eddie is face to face with him.

Richie has a curious look, and his eyes are twinkling with amusement. 

"You're completely dry down there. And I can tell nothings been up there for a while," Richie says. "Why'd you lie to me?" he asks it nonchalantly, like it's a joke. 

Eddie knows he has to tell Richie what he wants at some point, but he can't open his mouth. But when he sees Richie lean back to open the dresser drawer, pulling out a lube packet and condom, he finally says it.

“I fucking hate you.”

Okay, so maybe it's not the thing he was supposed to say, but at least he said something. 

Richie looks up at him, accidentally dropping the lube packet. He blinks once, confusion taking over his facial features. Usually when Eddie says something like that, Richie can tell he's joking. But this time, all he can see is actual rage in in Eddie's face. 

"Whoa baby, what'd I--" Before Richie can finish, Eddie kisses him, a bit too aggressively. He hooks his arms around his neck and grinds down on him, feeling the denim of Richie's jeans brush harshly against his soft thighs. 

Richie stays still, hesitantly kissing back, but then pulls away after a minute. He looks more concerned than aroused at this point, and Eddie can't really blame him. 

"Eds, are you okay?" he asks. "Look, we don't have to do this tonight, we can--" Richie is cut off again, but this time, with actual words.

"No! I'm fine, okay? I'm fucking fantastic! And we have to do this tonight because if we don't, I'm going to lose my fucking mind so can you just put your dick in me and stop being such an asshole?" 

Eddie realizes he really needs to take some anger management classes. And also some 'how to not be toxic to your boyfriend who you actually love very much' classes. 

It's Richie's turn to frown now.

"You don't think that's what I'm trying to do? If you stopped being such a little bitch then maybe I could finally prep you and then get on with it!" Richie's voice is raised now, and Eddie knows better than to interrupt him. Richie makes a frustrated noise, flipping them so that Eddie's ass hit the comforters, and he was on top of him.

"Baby, you're so fucking annoying, and I don't know what your problem is today, but I'm still somehow hard, so just shut up and let me finger you so I can give my cock some fucking release," Richie said as he grabbed the lube packet again. Eddie frowned up at him, and tried shoving the packet out of Richie's hands. He was trying to be as obvious as he could, but his dumb boyfriend wasn't getting the hint.

Richie shoved his hand away quickly, and Eddie reached out again. This time, Richie dropped the packet, but he also grabbed both of Eddie's wrists in one big hand, pulling him up harshly to look him in the eye.

Eddie whimpered a little, the grip on his wrists so tight that it was hurting. Richie didn't budge; he stared down at Eddie, an angry yet calm look on his face. It was like he was saying, _go ahead, do something, I dare you._

Eddie avoided his eyes, looking next to Richie's face and focusing on the little holes in his ceiling. His wrists were still clamped together in an steely hold, aching more now. He felt his cock dribble out pre-cum, throbbing a little.

Richie was quiet for minutes, and Eddie knew he was thinking--trying to figure out what was happening. The quiet made Eddie a little nervous, and he slowly looked into Richie's eyes finally, to try to figure out what Richie was thinking.

Maybe it was the embarrassment in Eddie's eyes, or maybe Richie noticed how Eddie wouldn't try to wiggle out of the painful hold, but in that exact moment, Eddie saw Richie piece it all together. His angry look was gone, replaced with realization. His mouth opened a little, and he began to smirk. 

"Oh baby," he breathed out. He looked down at the lube packet and back up at Eddie. He carefully picked it back up and placed it on the dresser slowly, watching Eddie's face for any signs of change. Eddie was blushing furiously now, and pulled Richie in for a kiss. He opened his mouth immediately and let Richie slide his tongue inside.

They made out for a couple of minutes before Richie pushed himself up to lean on his elbows. He fixed Eddie's hair fondly, pressing a small kiss on his forehead. 

"You gotta say it, Eds," Richie said. "I'm not doing anything until you say it." 

Eddie pouted. "Why?" He whined like a child. 

"Because I said so." Richie was giving him a warm smile, encouraging. Eddie didn't say anything for a few moments. Finally, _finally,_ he said in a small voice. 

"I want you to go in dry." It sounded ridiculous, even to his own ears, but he felt a weight lifted off of his chest as he said it. But Richie was relentless. 

"And?"

Eddie glared. He looked down again, shyly. "I don't want any prep either." He mumbled it, but he heard Richie inhale, letting out a breath. Eddie realized that Richie needed to hear him actually say it in order to make sure that was what he interpreted, rather than to just embarrass him.

Richie laid a hand on Eddie's hip, rubbing small circles in the pale skin.

"It's gonna fucking hurt, Eds." 

"Good. I need it to," Eddie said without hesitation. "And if I cry or scream or tell you to stop, just keep going."

Richie's eyes widened. "Eds, I don't think--"

Eddie placed his hand on Richie's wrist. "Please Rich, I want it, okay? I want it so fucking bad--and I'm not going to like, be mad at you or anything okay, I just...I need this, okay? Do it for me?" 

Richie was quiet, pondering at Eddie's words. He leaned over and planted a soft kiss against his lips. 

"I love you so fucking much, you don't even know," he said. Eddie felt his heart swell up with those words, and he opened his mouth to respond. Suddenly, Richie yanked his head back, biting into the neck of his skin and leaving a red mark. Eddie moaned, trying to take off Richie's shirt and clothes  _that he was still fucking wearing._

The minute his hands touched Richie's body, Richie grabbed them again and pinned his hands above his head on the bed. Richie used his other hand to reach down between them and hold Eddie's cock. It was slick with pre-come now, and Eddie moaned loudly, feeling Richie's rough hand enclose around the head. Richie rubbed at the slit, feeling more pre-cum squeeze out. 

Richie took the hand off of Eddie's cock and brought it up to his face. Keeping his hands pinned above his hands, he pushed his hips into Eddie's and shoved his wet fingers in Eddie's mouth and cheeks.

Eddie whimpered. The feeling of rough cloth on his sensitive cock made him dizzy with arousal. He was unable to touch anything, or do anything really--Richie's heavy weight keeping him still. And now Richie was making his face messy with his own pre-come, forcing Eddie to swallow most of the clear liquid on Richie's fingers. 

Richie grabbed his face with his damp fingers, pushing in Eddie's cheeks to open his mouth, and kissing him shamelessly. Eddie felt like an actual toy, letting Richie just do whatever he wanted to him. He was even more turned on now.

Richie suddenly pulled away and stripped off all his clothes-- _fucking finally_ , Eddie thought-- and then pulled Eddie's legs up to his shoulders. When cold air hit Eddie's exposed hole, he moaned and threw his head back. He felt so much anticipation and nerves in him, it was making him weak. Literally--like he couldn't move his limbs. His arms lay lax at his sides, and he couldn't move his legs, which were currently being maneuvered into the air and on Richie's shoulders. Suddenly, Richie paused. He looked around the room for something, finally seeing it and then quickly grabbing it.

Eddie watched him bring a black scarf from his closet. He was twisting it quickly, and before Eddie could ask what he was doing, Richie took both of Eddie's ankles and tied them together, tight. The bone was digging into the other, making Eddie wince at the pain. But even more pre-come dribbled out of Eddie's cock, and he moaned wantonly, throwing his head back and grinding his ass down the bed. He felt Richie's eyes on him all the while. 

Richie ducked his head through the opening between Eddie's ass and his tied ankles, leaning over the small boy again. Eddie's legs were now on top of Richie's shoulders, and he couldn't pull away; the tied scarf making him unable to move his feet or take them off Richie's shoulders. A shudder ran through his body again. 

Richie leaned in closer, grabbing both of Eddie's hands in each of his and pressing them down against the mattress, something he did every time they fucked. But they time, he raised them a little higher above Eddie's heads so he had more control. 

Eddie suddenly gasped, feeling the head of Richie's cock nudge his entrance. It scared Eddie, how big Richie felt next to his small opening. It felt like a banana nudging one end of a straw hole. 

Richie kissed Eddie then, passionately and desperately, pushing his tongue in to lick at Eddie's tongue. The second he pulled away from Eddie's mouth, he pushed his cock inside him.

Eddie screamed-- a loud, terrified scream, and felt tears immediately drop from his eyes. If he thought that night at the party was painful, he was so fucking wrong. This pain--it was blinding. Eddie felt his vision go black, and his head rolled to the side, fainting momentarily.

When he opened his eyes again, Richie was moving slowly, grunting quietly. Eddie immediately began crying loudly, and he twisted his arms, trying to pull out of Richie's grasp. But Richie held him there, only pushing down harder. He stilled his movements momentarily, and then began moving again. He had his face tucked into Eddie's shoulder, biting and breathing into the skin.

Eddie tried to push his legs away, but failed. He couldn't even scoot up or move any of his muscles. The searing sting and pain in his hole was all he could think about. It hurt so, so, so fucking much. Eddie whimpered and paused his breathing in an effort not to choke on his own sobs. He resumed again, and moving his face to the side, trying to move away from Richie. 

"P-p..please," he sobbed brokenly, not sure what he was asking for. He wanted Richie to stop, but he also didn't. Richie only acknowledged that second part, and drew back his hips almost all the way before slamming back in.

"Oh fucking hell baby, you're so fucking _tight!"_ Richie groaned into his shoulder, breathing heavily. Eddie whined and whimpered, body shaking like a leaf. Richie began to thrust harder now, filled with vigor. Richie put both of Eddie's wrists in one of his hands and placed the other on Eddie's hip, gripping the fleshy skin as he pounded into him harder. Eddie screamed again, the sudden change in speed intensifying the pain in his abused hole. And then he felt it--for the second time that week.

This time, he wasn't drunk, so he feeling was so much stronger. It began low in his stomach, but climbed up fast to the insides of his chest and his head. The pain was in the background again, just like that first night, but the pleasure was so much more. Eddie stopped crying, opening his mouth in an 'O' position, fluttering his eyes shut and panting like a dog. 

It was like he was filled with all this energy, but it had no where to go. So it just burst open in him, the heat and pleasure bouncing off of every nerve in his body. The heels of his feel tingled and his cock jumped up, an intense orgasm ripping through his entire body. He jolted up before completely going slack, unable to do anything except drown in the sheer pleasure filling his head.  The pain in his hole was like a dull ache, not really getting Eddie's attention anymore. He felt his face roll to it's side, and he moaned quietly, completely in bliss. He felt Richie letting go of his hands and gripping onto both sides of Eddie's hips, pulling him back to meet his thrusts, chasing his own orgasm eagerly. 

Eddie felt the hot, wetness fill him and Richie's loud grunt, and let his eyes close, completely wiped out from the whole night and the week's stress. He felt Richie pull out and whimpered at the harsh ache in his hole. It somehow hurt more than the last few minutes of Richie fucking him. Eddie felt another wave of arousal hitting his belly.

_Fuck_ , he thought.  _I am such a fucking freak._

**Notes for the Chapter:**

> hope you liked :)


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